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A new rapid multicomponent domino reaction for the formation of functionalized benzo[h]pyrazolo[3,4-b]quinolines
Authors:Jiang Bo  Zhang Ge  Ma Ning  Shi Feng  Tu Shu-Jiang  Kaur Parminder  Li Guigen
Institution:School of Chemistry and Chemical Engineering, Xuzhou Normal University, Jiangsu, PR China.
Abstract:A new multicomponent domino reaction for rapid and regioselective synthesis of highly functionalized benzoh]pyrazolo3,4-b]quinolines has been established. The reaction can be conducted by using readily available and inexpensive substrates under microwave irradiation within short periods of 10-26 min. Good to excellent chemical yields (61-91%) and complete regioselectivity have been achieved for 22 examples. Tedious work-up procedure can be avoided due to the direct precipitation of products from the reaction solution. The resulting benzoquinolines have been readily converted into quinoxaline-fused benzoh]isoxazolo5,4-b]quinoline analogues by treating with benzene-1,2-diamine under microwave irradiation. The structural assignment has been ambiguously confirmed by X-ray analysis. A new mechanism has been proposed for this new multicomponent domino process.
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